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Patented Nov. 24, 1931 UNFTED STATES A NT? OFFIC FRITZ GRETHER, OF BA SEL, SWITZERLAND, ASSIGNOR TO THE FIRM OF SOCIETYOF CHEMICAL INDUSTRY IN BASLE, OF BASEL, SWITZERLAND rnocnss non ,nYEIne. SILK jFAsT 'rrnrs No Drawing. Application filed Marchrl2, 930, Serial 110;435366, and in Switaefland March 16, 1 929.

The present invention. relates to a new processfor dyeing silk fast tints. It comprises the dyeing process and the material dyed according to the new process.

The dyeing of silk in neutral or fatty soap baths is a process which comes increasingly to the fore in the silk dye-house.

It has now been found'that complex metalliferous azo-dyestufis which may contain sev eral metals are excellently suitable for producing fast tints on silk in a bath the pH of which lies between 6.8 and 10. Particu-' larly suitable for the process are it among others those complex metal compounds which are derived from azo dyestuifs made by coupling diazo-compounds containing. lake- 'forming groups .and 'aminonaphthol com-.

pounds containing as many sO H-groups as naphthalene residues; which couplein orthoe position to theihydroxyl group, and which may be substituted at the nitrogen atom. Such products are inter alia the aminonaphthol-mono sulfonic acids and their deriva'- tives, such as-the urea or the dinaphthyl deing metals; such as aluminium Vanadium, chromium, manganese,-1ron, cobalt, nickel,

copper, zinc, etc.,as coming into consideration:

to produceVthese;;metal1iferous dyestufl'si The following examples illustrate the inventiomthe parts beingby Weight V Emamplel B t Sillnis. dyed withaddition of 10-20 per cent of crystallized sodium sulfate, thev goods being -entered at 60 C. and the bathheated gradually to 80-85"? C whereupon dyeing is continuedfor Ato 1 hour at this. temperature. .7 i

7 Example? r Ordinary or loaded silk is dyed with addition of 1+2grjams of Marseilles soap per litre and -30 per cent: of crystallized sodium sulfate, the goods'being entered at C. and the bath being heated gradually to -85 C;

whereafterzdyeing is continued for to 1 hour at this temperature. 1 i

Thefollowing table gives somegof the tints r obtainable according to thepresent invention rivatives of the 2: 5:? -a1ninonaphthol sulby dyeing in the manner described --in-Exfonlc acld. ample 1 or 2. i I No Diazotizing component Coupling component i Metal iTvint produced g V V onloadedsilk' 1 2-amjno-1-pheno1-4:G-disulfonic acid 2-amino-5-hydroxynarihthalene-Tsultonic acid- Cu Bordeauxil I .2 2- aminol-phenol 4z6-cdisulfonic acid and 4- 2-amino-5-hydtoxynaphthaleneW-sulfonic acid; Or+Cu Do.

'ch1oro-2-amino-I-pheno1. I a j i r 3 3 5-nitr0-2-amin0-1-phenol Z-phegylamino-fi-hydroxynap1itha1ene 7-su1fonic CL, Greo'nishu I V ac1.. 4 D0 -i. do ;i Gr +Cu Blue. 5 Do dn i C11 Blue-violet.- 6 Anthranilic acid do w Cu Violet. i 7 4-chloro-2-amino-l-phenol Zaceiylamino-5-hydroxynaphtha1ene-7-su1ionic Cu 'Red-violet Y Y ,ac1.- r y 2 's 'Dichloro-2-aminoJ-pheno1 I 2 benzoylamino 5 hydroxynaphthalene 7- Cu. Red-violet.

. i su1fonicacid.-, n 9 5-nitro-2-amino-1-phenol do Gr Green-grey. 10 2 mol of 2-amino-1-phenoI-4-sul[amide 2:2-1;1inapht 1y1amine 5:5'- ,dihydroxy 7:7-di- 2 Cu Violet.

su omc aci r 11 2 mol of 2-an1ino-1-pheno1-4-su1famide Ureadof2-amino-541ydroxynaphtha1ene-7-su1f0nic Ct+ Cu..- Brown-violet. 12 2mo] of 4chl0r0-2-amin0-l-phenol Azo-dyestuff from'diazotizcd 2-amino-5 -hydroxy-i 0L]. 'G'rey p and 2 amino- 5 hydroxynnphthelone-7-sul- 7 a fonicacid. V j 13 5-nitro-2-amin0-1-pheno1 1-amino-8-hydroxynaphtha1ene-4-su1tonic acid- .i Cu' Green.

Particularly chromium and copper Z are There must be named. also" assuitable ,forfl.

pointed out among the known complex-formthe invention among others metal compounds- Q fonic acid, 2-amino-8-hydroxynaphthalene 6- of dyestufis obtained from the following diazo components: diazotized nltro l 7 chl0ro-2-amino-1-phenol, 4-chloro-2-a'rninol-phenol-G-sul-fonic acid, .4-nitro-2-amino-lphenoltS-sulfonic acid, 6 nitro 2'- amino-1- phenoll-sulfonic acid, picramic acid, parav aminosalicylic acid, and coupling compodichloro) -benzoylamino -5 hydroxynaphthav lene-7-sulfonic acid, 2(3-nitro) -benzoylami- 110-5-hydroxynaphthalene-7-sulfonic" acid, 2-

benzoylamino 8 hydroxynaphthalene 6- sulsulfonicacid, 1 amino 8 hydroxyna'phthalen'e-al-sulfonic acid, 1-benzoylamino-8hymany'SO H-groups as naphthalene residues, 7

droxynaphthalene-e-sulfonic acid, l-phenylamino-; 8 hydroxynaphthalene 45- sulfonic 1 acid, 2-acetylamino-8-hydroxy naphthalene- 1. A process for the production of fast tints on silk,consisting in treatingsilk in a bath the pH of which lies between 6.8and 10,

with complex metal compounds which are V a I v V I whereinRmeansahydrogen'atom,aryl,alkyl 1 derived from azo-dyestuffsmade from diazocompounds containing lake-forming groups and aminonaphthol compounds containing as many SO H-groups as naphthalene residues, and which couple in ortho-position to the hydroxyl group. V

2 A process forthe production of fast tints on silk, consisting'in treating silk in a bath the pHof which lies between 6.8 and'lO,

' with compounds of complex metals the atomic atomicw'eight of which lies between 52 and 64 which are derived from azo-dyestuffs made from 'ortho-hydroxy diazo-components" and aminonaphthol compounds containing as and which couple in ortho-position to the hydroxyl group.

process tints on sillgconsisting', in treatingsilk in a bath the pH of which lies between;6.8 and 10, with compounds of complex metals the atomic weightof which lies between 52 and 64 which are derived from azo-dyestuffs made from ortho-hydroXy-diam-components and amino-naphthol "mono-sulfonic acids which couple in 'orthopositiion to the hydroxyl groups.

' 45A tints on silk, consisting'in treating silk'in a bath thepH of which lies between,6.8 and 10, with compounds of complex metals the atomic weight of, which lies between 52 and .64 whichiare derived from azo-dyestulis made for the production of fast:

'fonicacid of the general formula process for the production of fast from' ortho-hydroXy-diazo-components and an aminonaphtholmono sulfonic acid of the general formula r v y 7 v wherein R stands for H, alkayl, aryl, aralkyl 'or acidyl, y in one case stands for an OH- group and in the other case for a hydrogen atom, a in one case stands for an SO H- I compounds of complex metals the atomic weight of which lies between 52 and 64; which are derived} from; a'zo dyestuffs made from ortho hydroky-di'azo-components and a 2- amino- 5 -hydroxynaphthaleneeT-sulfonic acid -or the "general formula or aralkyl. V I 6. A process for the production of fast tints which are derived fromazo-dyestuifsimade from ortho-hydroxy-diazocomponents and a. 2-amino-5-hydroxynaphthalene-7-sulfonic acid of the general formula flossml l lt wherein R means a hydrogenatom, arylor aralkyl. 1 r v- 1 7. A process for the production of fast tints on silk, consisting in treating silkin a fatty soap bath with compounds of chromium and copper which are derived fromazo-dyestuifs V 7 made from ortho-hydroXy-diazo-components and a FZ-amino-5-hydroXynaphthalene-7-sul Incaswherein Rvm-eans a hydrogen atomor aryl.

tints 0n silk, consisting in treating silk in a fatty soap bath with a chromium compound which is derived from an azo-dyestuff made from ortho-hydroxy-diam-components and 2-amin0- 5 hydroxy naphthalene- 7 -sulfonic acid of the formula In witness whereof I have hereunto signed i my name this 28th day of February, 1930.

FRITZ GRETHER. 

